Vacation rentals in Street

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Top-rated vacation rentals in Street

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Middle River

4.95 out of 5 average rating, 37 reviews

Waterfront Home with Private Beach, Stunning Views

Escape to paradise at our Chesapeake Bay waterfront vacation home in Oliver Beach! Our home is the ideal place to unwind and appreciate the beauty of Chesapeake Bay. You'll love the stunning views, the private beach, the spacious upper deck and the beachside deck surrounded by trees. You'll have so much fun fishing, swimming, kayaking, paddle boarding, or just relaxing by the water! It's the perfect spot for a dreamy retreat, a romantic sojourn, or for shared fun with group of friends or family.

Guest favorite

Apartment in Leacock-Leola-Bareville

5 out of 5 average rating, 50 reviews

Dreamwood on main w/ hot tub + toy room for kids

Make memories with your whole family at this beautiful cozy place . You are at a convenient location right along Main Street (Route 23 ) with lots of places to visit near by . Our patio has a grill, a hot tub, and picnic table with extra seating , a perfect place for a relaxing evening outside . Our fully functioning kitchen will make cooking meals easy . And the basement has a kids play area and a foosball table . We hope you might enjoy the space as much as our family does .

Guest favorite

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Guest favorite

Home in Centreville

5 out of 5 average rating, 22 reviews

Water Oasis on the Eastern Shore

With incredible views of the Corsica River from almost every room and set on 6 acres amidst idyllic farms, your home away from home calls. A 5-bedroom, 6.5-bath waterfront oasis, Middle Fox Cove is the key to unlocking a memorable getaway you will never want to leave behind. This 5000 square foot home is a tranquil masterpiece that makes room for relaxing and recreating. Bring the entire family or just a quiet retreat for two - make this the memorable experience you’ve been looking for.

Superhost

Cottage in Pasadena

4.88 out of 5 average rating, 121 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Guest favorite

Cottage in Wrightsville

4.94 out of 5 average rating, 100 reviews

Stone Cottage at Roundtop Estate (Couples Retreat)

Want a Unique Winter Getaway!! with a Hot Tub/Fireplace, and Espresso Machine! Come experience this stunning cottage and cozy up beside the massive fireplace!! (gas burning) Where to start? From the architecture to the luxury furnishings, to the woods surrounding it, to the hot tub, to the Gas burning fireplace to sit beside your loved ones while drinking your latte that you can make by using the espresso machine, An oasis!

Guest favorite

Home in Gap

4.9 out of 5 average rating, 126 reviews

Dream View

Welcome to our beautiful 3 bedroom,2 bath home with an attached 1 bedroom,1 bath apartment that’s perfect for families or groups who value privacy and convenience. Enjoy breathtaking views of the picturesque surroundings right from the comfort of your home or bask in the serene atmosphere of the big backyard where you will possibly see wildlife. The hot tub is an added bonus,perfect for a relaxing evening under the stars.

Guest favorite

Guesthouse in Owings Mills

4.97 out of 5 average rating, 114 reviews

The Garden Studio

Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.

Guest favorite

Home in East Earl

4.89 out of 5 average rating, 111 reviews

Cottage On Main-cozy 3/1.5 near Shady Maple

Escape to this peaceful haven surrounded by picturesque Amish farmland. This 3-bedroom, 1.5-bath retreat is thoughtfully designed to make you feel at home. Cook in the fully stocked kitchen or savor local takeout. Start your day with coffee on the front porch, observing the charming buggies passing by. Experience serenity and comfort in this idyllic rental, perfect for a relaxing family getaway.

Guest favorite

Apartment in Betterton

5 out of 5 average rating, 15 reviews

Bayside Bungalow

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps the beach, where you have a picnic pavilion, beach volleyball, and BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.

Guest favorite

Home in Essex

4.81 out of 5 average rating, 78 reviews

Sunset Haven on Sue Creek

Unparalleled Sunsets on the Water! This unique simple renovated cottage, offers an amazing waterfront experience with a private sandy beach, amazing nightly sunsets and a 60 foot pier which can hold most vessels up to 45 feet. Owners are very friendly live next door and are happy to help make your relaxation complete.

Guest favorite

Home in Elkton

4.93 out of 5 average rating, 57 reviews

Waterfront Sunset River Cottage -perfect getaway

This waterfront romantic nautical cottage will not disappoint. Beautiful sunsets all year round. And the water views are amazing… perfect for a romantic getaway or a weekend with friends